Imidazole → Silane, (4-bromophenoxy)(1,1-dimethylethyl)diphenyl-

HRID 1757364Notes

Reaction equation

HRID 1757364 reaction equation
N1C=CN=C1.[C:6]([Si:10](Cl)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:9])([CH3:8])[CH3:7].[Br:24][C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=1.C(=O)([O-])O.[Na+]>C(N(CC)C=O)C.CN(C)C=O>[Si:10]([O:31][C:28]1[CH:29]=[CH:30][C:25]([Br:24])=[CH:26][CH:27]=1)([C:6]([CH3:9])([CH3:8])[CH3:7])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 78084-BromophenolHCID 94078tert-ButyldiphenylchlorosilaneHCID 516892Sodium Bicarbonate

Product 1

HCID 11292808Silane, (4-bromophenoxy)(1,1-dimethylethyl)diphenyl-Yield 0.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 12051DiethylformamideSolvent

Procedure

11.06 g (162.5 mmol) of imidazole in 30 ml of diethylformamide are added dropwise at room temperature to 35.24 g (130.0 mol) of tert-butyl-chlorodiphenylsilane and 11.25 g (65.0 mol) of 4-bromophenol in 150 ml of dimethylformamide. After the reaction mixture has been stirred at room temperature for one hour, it is poured into 1000 ml of 5% strength by weight aqueous sodium hydrogencarbonate solution and extracted twice with 400 ml of dichloromethane, and the organic phase is washed with aqueous sodium chloride solution, dried over sodium sulfate, filtered and evaporated to dryness. Chromatographic purification (silica gel/hexane: ethyl acetate 8:2) gives 23.40 g of 4-bromophenyl tert-butyldiphenylsilyl ether. ##STR29##

Workup

  1. extractionextracted twice with 400 ml of dichloromethane
  2. washthe organic phase is washed with aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customChromatographic purification (silica gel/hexane: ethyl acetate 8:2)

Sources & evidence

ORD record
ord-11b5905337874a6185812d5245159f69
Source dataset
uspto-grants-1995_08
Patent number
US05445763

Reaction notes

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